US4124724AExpiredUtility

Crystalline caffeic acid derivatives and compositions and method for treating snakebite

60
Individually held — no corporate assignee on recordPriority: Dec 8, 1975Filed: Nov 29, 1976Granted: Nov 7, 1978
Est. expiryDec 8, 1995(expired)· nominal 20-yr term from priority
Inventors:John W. Agoro
C07C 59/52
60
PatentIndex Score
11
Cited by
3
References
24
Claims

Abstract

Novel crystalline products of manufacture are represented by the formula: ##STR1## wherein R 1 and R 2 are selected from the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R 1 and R 2 can be hydroxyl, and the pharmaceutically acceptable salts of the indicated compounds. The compounds are useful as anti-venom agents for hemolytic snake venoms. Pharmaceutical preparations containing the above compounds, or the compound commonly known as caffeic acid wherein both R 1 and R 2 are hydroxyl, are provided for treatment of snakebite victims, as well as the method of using those preparations in such treatment.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A crystalline product of manufacture of the formula: ##STR5## wherein R 1  and R 2  are selected from the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R 1  and R 2  can be hydroxyl, and the pharmaceutically acceptable salts thereof. 
     
     
       2. A crystalline product in accordance with claim 1 of the formula: ##STR6## and the pharmaceutically acceptable salts thereof. 
     
     
       3. A crystalline product in accordance with claim 1 of the formula: ##STR7## and the pharmaceutically acceptable salts thereof. 
     
     
       4. A crystalline product in accordance with claim 1. that is a mixture of compounds of the formula: ##STR8## and the pharmaceutically acceptable salts thereof. 
     
     
       5. A crystalline product in accordance with claim 1 of the formula: ##STR9## and the pharmaceutically acceptable salts thereof. 
     
     
       6. A crystalline product of manufacture consisting of a member selected from the group consisting of caffeoyl caffeic acid, decomp. 135°-140° C., and the pharmaceutically acceptable salts thereof. 
     
     
       7. A crystalline product of manufacture consisting of a member selected from the group consisting of 3-hydroxy-4-(3',4-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof. 
     
     
       8. A crystalline product of manufacture consisting of a member selected from the group consisting of 4-hydroxy-3-(3',4'-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof. 
     
     
       9. A crystalline product of manufacture consisting of a member selected from the group consisting of 3,4-di-(3',4'-dihydroxycinnamoyl)-cinnamic acid and the pharmaceutically acceptable salts thereof. 
     
     
       10. A pharmaceutical preparation suitable for oral or parenteral use comprising a therapeutically effective amount of anti-snake venom drug selected from the group consisting of a crystalline product of manufacture of the formula: ##STR10## wherein R 1  and R 2  are the same or different members of the group consisting of hydroxyl and the caffeoyl group, with the limitation that only one of R 1  and R 2  can be hydroxyl, a mixture of said products, and pharmaceutically acceptable salts of said products, together with a pharmaceutically acceptable carrier or diluent. 
     
     
       11. A pharmaceutical preparation in accordance with claim 10 compounded for oral use. 
     
     
       12. A pharmaceutical preparation in accordance with claim 10 compounded for parenteral use. 
     
     
       13. A pharmaceutical preparation in accordance with claim 10 wherein said crystalline product of manufacture is 3-hydroxy-4-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof. 
     
     
       14. A pharmaceutical preparation in accordance with claim 10 wherein said crystalline product of manufacture is 4-hydroxy-3-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof. 
     
     
       15. A pharmaceutical preparation in accordance with claim 10 wherein said crystalline product of manufacture is 3,4-di-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof. 
     
     
       16. A pharmaceutical preparation in accordance with claim 10 wherein said crystalline product is caffeoyl caffeic acid or a pharmaceutically acceptable salt thereof. 
     
     
       17. A pharmaceutical preparation suitable for oral or parenteral administration to a mammalian snakebite victim comprising from about 0.03 to about 3.5 mg. of 3,4-dihydroxycinnamic acid or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier or diluent. 
     
     
       18. A pharmaceutical preparation in accordance with claim 17 wherein the trans isomer of 3,4-dihydroxy cinnamic acid is present in a dosage of from 0.03 to about 3.5 mg. 
     
     
       19. A method of inhibiting the hemolytic action of snake venom comprising administering to a mammalian snakebite patient a therapeutically effective amount of anti-snake venom drug selected from the group consisting of a crystalline product of manufacture of the formula: ##STR11## wherein R 1  and R 2  are the same or different members of the group consisting of hydroxyl and the caffeoyl group, a mixture of said products, and pharmaceutically acceptable salts thereof. 
     
     
       20. The method of claim 19 wherein said anti-snake venom drug is 3-hydroxy-4-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof. 
     
     
       21. The method of claim 19 wherein said anti-snake venom drug is 4-hydroxy-3-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof. 
     
     
       22. The method of claim 19 wherein said anti-snake venom drug is 3,4-di-(3',4'-dihydroxycinnamoyl)-cinnamic acid or a pharmaceutically acceptable salt thereof. 
     
     
       23. The method of claim 19 wherein said anti-snake venom drug is caffeic acid or a pharmaceutically acceptable salt thereof. 
     
     
       24. The method of claim 13 comprising treating said snake-bite patient with a total of from 0.03 to 3.5 mg. of caffeic acid or a pharmaceutically acceptable salt thereof and thereafter discontinuing treatment for at least one month.

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